Red Carpet Flashback! These Photos from The Holiday Press Tour in 2006 Will Make You Nostalgic

This holiday season, we look back at tailoring choices from Holiday press tour, where the film’s stars Jude Law, Cameron Diaz and Kate Winslet hit the carpet in glamorous outfits fit for a Hollywood event and festive Christmas party (of course).

There’s a lot to dissect with the cast’s ensembles during the 2006 press tour (those were different times, after all), but the overarching theme seems to be business-casual glam.

For the film’s November 29, 2006 release, the trio (who star in the Nancy Meyers classic alongside Jack Black and Eli Wallach) coordinated in gold and black.

Cameron Diaz, Jude Law and Kate Winslet at the premiere of “The Holiday” in New York on November 29, 2006.

Lawrence Lucier/FilmMagic

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Diaz, who famously played Hollywood executive Amanda Woods, wore a 2000s signature gold floral mini dress with flutter sleeves and a two-tone metallic ruffle hem. Her hair also went from blonde to a darker brunette, but her trendy bangs remained the same.

She wasn’t the only one who changed her look after filming. Winslet, who played journalist Iris, changed her reddish blonde hair to a light golden hue, which stuck out against her satin all-black skirt.

Law, in charge of the ever-charismatic Graham, dressed in a black two-piece suit, with a striped tie and a white button-down shirt with a contrasting black collar (complete comeback).

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Cameron Diaz, Jude Law and Kate Winslet teamed up in black ensembles for the “Holiday” premiere in London.

Fred Duval/FilmMagic

On December 5, the stars flew to London on Rest premiered there, and this time they coordinated in black combinations with Diaz in a floor-length halter dress with a metallic sheen and Winslet in a mini velvet outfit with bows and tulle. Law wore a gray blazer and sheer vest over a collared shirt.

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Of Holiday hit theaters 18 years ago, there were several behind-the-scenes secrets revealed by the cast and crew that made it a perennial talking point.

In an interview on November 24 for BBCLaw mistakenly breaks the spell of the idyllic Cotswold lifestyle the film is known for by discovering that Amanda’s cottage (which originally belonged to Graham’s sister Iris) isn’t real at all.

“That little house doesn’t exist,” Law admitted. According to the actor, director Meyers couldn’t find the perfect house, so she decided to rent land and build a cozy home from scratch.

Cameron Diaz, Jude Law and Kate Winslet.

E. Charbonneau / staff / Getty

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“This is a funny thing, if you watch it… We shot here in the winter. And every time I walked through that door, we would cut, and we shot the interiors in LA about three months later,” he added.

Long before it was even time for our annual Rest look again, Law told E! News in June that he “likes the idea” of a potential sequel to the classic. He teased the prospect alongside Meyers in an Instagram video re-enacting his famous Mr. Napkin Head.

Earlier this month, costume designer Marlene Stewart, who donned the set, shared with PEOPLE exclusively some fun details about the iconic look featured in the film, from Amanda’s quietly luxe ensemble (which was ahead of its time) to Iris’ sporty leisure ensemble.

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